Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent

Definitions

• the present invention relates to new salicylanilides that are distinguished by a superior bactericidal action.
• the present invention relates to salicylanilides containing at least two trifluoromethyl substituent radicals that have the general formula I co-NH 1' 'jln (FBC R2 OH in which R represents a radical of the group consisting of hydrogen, chlorine, bromine and nitro, R represents a radical of the group consisting of hydrogen, chlorine and bromine, R represents a radical of the group consisting of hydrogen and chlorine, and m and n are integers from 0 to 2 whose sum is at least 2 and not more than 3.
• R represents a radical of the group consisting of hydrogen, chlorine, bromine and nitro
• R represents a radical of the group consisting of hydrogen, chlorine and bromine
• R represents a radical of the group consisting of hydrogen and chlorine
• m and n are integers from 0 to 2 whose sum is at least 2 and not more than 3.
• Salicylanilides having bactericidal activity which contain at least 3 halogen substituents are disclosed in United States Patent No, 2,703,332.
• the activity of, for example, 3,4,S-trichlorosalicylanilide and the corresponding 4,5- dichloro-3-trifiuoromethylsalicylanilide against Staphylococcus aureus is disclosed in that patent.
• salicylanilides having the above general formula containing at least two trifluoromethyl groups are considerably more effective as bactericides than the products disclosed in that patent and especially more effective than the compound described therein having only one trifluoromethyl substituent in its anilino radical.
• This difference in activity is not only in degree but also in kind as may be seen from a comparison of the bactericidal actions of the known compounds against Staphylococcus aureus and Escherichia coli and the bactericidal action of the new products of our invention.
• 3',4',5-trichlorosalicylanilide and 4,5-dichloro 3 trifluoromethylsalicylanilide disclosed in Patent No.
• 2,703,- 332 have only a moderate action against Staphylococcus aureus and an insuflicient action against Escherichia coli, the products of our invention generally possess a substantially greater activity against Staphylococcus aureus and a surprisingly great activity against Escherichia call.
• the methods for preparing prior known salicylanilides can be used such as that described for the preparation of salicyl-o-toluide, for example, by C. F. H. Allen and J. Van Allan in Organic Synthesis, vol. 26, John Wiley & Sons, Inc., New York, 1946, pp.
• halides of salicylic acids are used for the production of the salicylanilides, it is not necessary to first produce these halides separately.
• the condensation may rather be carried out by heating the salicylic acids together with the arylamines in an inert organic solvent, such as monochlorobenzene, toluene, nitrobenzene, etc., while adding a stoichiometrically equivalent amount of an inorganic acid chloride, such as phosphorus trichloride or thionyl chloride (S0012).
• an inert organic solvent such as monochlorobenzene, toluene, nitrobenzene, etc.
• the salicylanilides according to our invention containing at least two trifluoromethyl groups are excellent disinfectants, especially when used for sanitation purposes. They may be employed as such in the control of bacterial infectious diseases of the skin, or when incorporated into the conventional washing agents, cleaning agents, detergents and cosmetics, they may also be employed in the disinfectant cleaning of objects of all kinds, such as textile materials, apparatus, equipment and containers in the beverage industry, milk cans, etc.
• Example 1 248.5 parts of S-chlorosalicylate together with 229 parts of 3,5-bis(trifluoromethyl)aniline are heated to 190200 for 5 hours with stirring. Then the evolved phenol is distilled off at a subatmospheric pressure and the light yellow-colored residue is recrystallized from chlorobenzene.
• the 5-chloro-3,5'-bis (trifluoromethyl)salicylanilide is thus obtained in a nearly quantitative yield in the form of coarse, colorless prisms having a melting point of 179-181.
• Example 2 206 parts of 4-trifiuoromethylsalicyclic acid are stirred with 161 parts 3-trifluoromethylaniline and 1000 parts by v-olumeof monochlorobenzene. This mixture is admixed at room temperature with 50 parts of phosphorus trichloride in parts by volume of monochlorobenzene and heated under reflux for about 1 hour at the boil. Meanwhile the 4-trifiuoromethylsalicylic acid dissolves gradually. After the evolution of hydrogen chloride has ceased, the hot ichlorobenzene solution is poured off from the precipitate which consists of phosphorous acid and filtered.
• Percentage kill Escherichia coli Staphy- ZOcoccus aureus Testing of the compounds with respect to their bactericidal action is carried out as follows: A 24-hour culture of the test organism (Staphylococcus aureus or Escherichia coli) is diluted to a concentration such as to produce an inoculum each milliliter of which has a bacterial count of 50,000,000 organisms. One-tenth of a milliliter of this inoculum is then added to a tube of broth containing the test compound at a concentration of 10 gammas (mi-crograms) per milliliter. The inoculated tube is then incubated at 37 for 10 minutes.
• R is a radical of the group consisting of hydrogen
• R is a radical of the group consisting of hydrogen
• n and n are integers from 0 to 2 whose sum is at least 2 and not more than 3,

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Detergent Compositions (AREA)

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Cited By (17)

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  • BE BE615511D patent/BE615511A/xx unknown
• 1961
  • 1961-03-25 DE DEC23741A patent/DE1167328B/de active Pending
• 1962
  • 1962-03-23 CH CH347362A patent/CH421930A/de unknown
  • 1962-03-23 US US182096A patent/US3332996A/en not_active Expired - Lifetime
  • 1962-03-23 SE SE3284/62A patent/SE301467B/xx unknown
  • 1962-03-23 GB GB11218/62A patent/GB930950A/en not_active Expired
  • 1962-03-23 DK DK135662AA patent/DK102957C/da active

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